Moonlight Serenade
by Lolsome-o-sis girl
Summary: [Dean/Castiel] In which Charlie comes up with an elaborate plan to get Dean and Castiel together, and coerces Sam into joining forces with her. It maybe doesn't end too terribly.


**Moonlight** **Serenade**

 _Fandom: Supernatural_

 _Rating: T_

 _Genre: Romance, Humor_

 _Pairing: Dean/Castiel_

 _Word count: 2924_

 _Summary: In which Charlie comes up with an elaborate plan to get Dean and Castiel together, and coerces Sam into joining_ _forces with her_ _. It maybe doesn_ _'_ _t end too terribly. Dean/Castiel ONESHOT._

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 **AN: Spawned from the idea that Charlie and Sam would be the ultimate** **matchmakers for Cas and Dean. I have no idea where/if this would fit in terms of** **canon, but I hope you all enjoy anyway.**

 **Master of madness, cheers for reading this for me :).**

* * *

 **DISCLAIMER. I do not own Supernatural.**

* * *

Dean almost spat out his mouthful of pie. " _Prom_ -!?"

Charlie, who had voiced the idea, nodded seriously. "Yeah. Prom."

It must have been the worst idea he'd ever heard. "Of _all_ the things - Prom - !"

"What is so bad about prom?"

The piece of pie nearly left Dean's mouth for a second time. "What's so bad ab - ? Where do you want to _start_?"

Sam let out a snort. "Just because you have some kind of phobia of anything that requires friendly interaction that won't definetly lead to sex."

"Bitch."

"Jerk."

Charlie rolled her eyes at the brothers' usual insult exchange. "Oh, come on, why shouldn't we have a prom? Did either of you even go to your own high school prom?"

"Nope. Dropped out before then." Dean smirked impishly. "Sammy went, though."

"Only because _you_ told everyone that I was taking Elise Breckham to prom!" Even now, Sam looked mortified by the memory of Elise Breckham's eager expression as she babbled about how excited she was about going to prom with him whilst his twenty two year old brother tried - and failed - to hide his smug grin behind his packet of crisps.

"You coulda backed out," Dean said, also thinking back on that eventful day for teenage Sam. It brought a smirk to his face even now.

"No, I couldn't," Sam replied, but the expression on his face made it seem as though he partly wished, in retrospect, that he had; this wasn't lost on Charlie. The redhead beamed triumphantly.

"See? Between the pair of you, you either didn't bother going to prom, or you had a terrible night."

"It wasn't _so_ bad -" Sam began, but Charlie cut him off.

"Yeah, yeah, yeah, you know what I mean. My point is, none of us experienced the fairytale high school prom that the movies always promised us -"

"Who would want to experience that amount of torture?" Dean muttered.

The redhead ignored him. "- which is why we should have our own prom. Right here." She gestured to the library around them, one of the many rooms in the bunker. "I mean, it's not as if space is going to be a problem. The bunker's huge, after all." Neither Sam or Dean looked particularly convinced by her enthusiasm, so she ploughed on. "Come on, it'll be fun! We can do our own thing. Make it special, you know?"

"You know that we're not teenagers anymore, right?"

"What does that matter?" Charlie's brow furrowed. "Stop trying to get out of this, Dean!"

"Okay, okay, well, let's pretend that this really is a good idea...Isn't the whole point of prom taking dates?" He raised an eyebrow in his brother's direction. "I mean, dude, you're not exactly my type."

Sam gave him one of his bitch faces, not sure whether to be relieved or mildly offended by this information. Charlie, on the other hand, was smirking.

"Oh, I don't know, Dean. Why don't you ask Cas to be your date?"

Dean's eyes narrowed as the two others at the table began snickering amongst themselves. "Shut up."

"Are you blushing, Dean?" Sam grinned. His brother could be so transparent at times.

"Pipe down, Samantha," Dean growled, rising from his seat and stalking out of the room, mumbling "I'm getting another beer," over his shoulder.

Sam turned to Charlie when he was sure that his brother was out of earshot. "You're planning something, aren't you?"

"Why, Sam," Charlie replied, her face the picture of innocence. "I don't know what you're talking about..."

* * *

When Dean awoke the next morning, he hoped against hope that Charlie would have forgotten all about her chick-flick notion of holding a prom right there in the bunker. He soon discovered, however, when he stumbled into the kitchen in search of a hangover cure, that he was sorely mistaken.

Charlie and Sam had certainly been busy whilst he'd been blissfully unaware of everything. The corridors of the bunker were now adored with paper streamers, and strings upon strings of plastic fairy lights that looked like they belonged more on a Christmas tree than anywhere else. The kitchen had also had a similar makeover, the walls almost invisible under the streamers, the table cluttered with bags from the nearby grocery store. Dean sneaked a look inside one of them, his interest sparked when he noticed the pie hidden at the bottom of the bag; Sam whipped the supplies off the table before his brother could get his hands on anything. Charlie shook her head.

"Dean! It's not for now. It's for _prom_!"

The elder Winchester pulled a face. "You're not seriously still going ahead with this prom thing, are you?"

"Of course! Speaking of which -" She produced an A5 piece of card from her pocket and handed it to Dean.

"What the hell is this?"

"Your invitation."

Dean exhaled loudly. " _Charlie_..."

"We have to do this properly, Dean!" She insisted.

"Properly? It just says, _**Dean, don't even think about trying to get your ass out of this**_ _ **.**_ "

"I figured you'd rather the direct approach." Charlie gave a half-shrug, sharing a look with Sam. "Have you figured out how you're going to ask Cas to be your date yet?"

The uncomfortable scowl from the night before was back on Dean's face. "He's not my date."

"Well, _obviously_ , because you haven't asked him yet!" Charlie rolled her eyes.

"And I'm not _going_ to ask Cas!"

"Ask Cas what?"

Dean leapt out of his seat and all but threw himself across the room; he let out a sigh and sank back down when he saw who it was.

"Dammit, Cas, we've talked about that." Yet again, the angel had managed to silently sneak up on him without him realising and scare the crap out of him.

"My apologies," Cas replied, before repeating his earlier question. "What did you want to ask me?"

Dean looked uncomfortable again. "Nothing. Don't worry 'bout it."

"Very well." Cas nodded, before he turned to address Sam. "Are you aware that it is only July and that you are decorating up for the Christmas season six months earlier than is custom?"

So, Dean wasn't the only one who thought it looked like Christmas, then.

Sam smiled at the angel. "No Christmas, Cas. Just prom."

"Prom?" Cas tilted his head to the side, the same thing he always did whilst frowning in confusion. "What is a prom?"

Whilst Charlie got Cas caught up on all things related to prom, Sam caught Dean's gaze, eyebrow raised; ever since they were kids, they had worked out a way to silently communicate so that others could not pick up on it. It came in handy when they were working a job and others were in the room. It appeared that now was a good time to put that into practise.

Sam nodded his head ever so slightly towards Cas, giving his brother a questioning look, which roughly translated as, _Why won't you ask Cas to prom?_

Dean gave his head the tiniest shake before rolling his eyes. _We're just friends._

 _So? I'm going with Charlie. Technically._ The implied _technically_ appeared to have been added as an afterthought, to reassure his older brother.

 _Seriously?_ Dean's eyes widened slightly.

 _Yep._ Sam nodded once, before his eyes flickered to Cas again, as a way of trying to say, _Go on! Ask him!_

Dean let a sigh escape him. Arguing with his little brother was pointless; he would never let something drop. Charlie and Cas were now both glancing in their direction.

"Are you guys doing your special brother telepathy thing again?" Charlie asked, eyebrow raised, fixing Sam with a hard stare. "You'd better not be giving him any ideas."

"As if I would."

Her eyes narrowed, analysing Sam's innocent expression. "Outside." She nodded towards the door. "I need to speak to you."

Dean smirked. _Looks like you're about to get dumped, Sammy._

Sam glared at his brother, mumbling "Jerk" under his breath, following Charlie out of the room.

"Let me guess," he said, once they were a safe distance away from the kitchen. "You're planning something, and now you want my help."

"We need to combine forces." Charlie nodded back the way they had come. "To get those two lovesick fools in there to stop being so blind. I mean, the UST is getting painful."

"Wait - is that what this whole prom thing is all about?" Sam's face broke out into a smirk. "Is this whole thing just an elaborate matchmaking scheme to get Cas and Dean together?"

Charlie shrugged. "What else was it going to be for? I'm hardly someone who was _dying_ to go to prom back in the day. So, what do you think? Work together?"

Sam grinned. Charlie was right - the UST between his brother and the angel was becoming unbearable at times. It was about time someone did something about it. Besides, now, at least, he had compensation for the Elise incident with his own high school prom.

"What the hell. Let's do it."

* * *

"Poetry?"

Charlie nodded, sticking another post-it note onto Cas' door. "Yeah. Poetry. Who can resist poetry?"

Sam pulled a face, brows knitted together. "Dean isn't the type to write poetry. I think he would rather drive his precious impala into a tree more than once than write poetry."

"Love makes you do weird things, Sam. Some climb a mountain. Some cross a river. Dean Winchester supposedly writes poetry." She smiled at their handwork, at the neat lines of post-it notes, each with a word on, forming the small poem.

 _ **I'm no good saying my words to the angel in the trenchcoat,**_

 _ **So I wrote them down on these post-it notes,**_

 _ **Bringing you, Cas, a message from Dean,**_

 _ **Will you go to the prom with me?**_

"One of your better verses, I think." Charlie turned to grin at her accomplice. "When did you get so poetic?"

Sam gave a shrug. "I may or may not have written Jessica poetry once or twice over the years to win her over."

"Did it work?"

He smiled at the memory. "Rather well, actually. After a while. Once I got past the awkward first attempts."

"Hopefully history will repeat itself, then." The redhead beamed at their handiwork. "What do you think? You think Cas'll like it?"

"Cas likes anything to do with Dean." Sam rolled his eyes. "But we'd better hide in case we get caught. Not sure Dean will appreciate this, given his denial."

"That won't happen!" Charlie said confidently, as the pair of matchmakers headed towards the library in order to get out of the way. They didn't get very far. Charlie had only just slid into her seat, before "Sammy!" echoed down the corridor and, a few moments later, Dean appeared in the doorway, a collection of pink post-it notes crumpled in his hand and a brooding scowl on his face that darkened when he locked eyes with his little brother, who was pretending to bury his nose in one of the many books lying around.

"You. A word. _Now._ "

Sam exchanged a look with Charlie, who simply shrugged and smiled, as if this had all been a part of her plan. Come to think of it, Sam reasoned, as he followed Dean out of the room, she probably _had_ planned this.

"What's up?"

Dean pushed the crumpled pile of notes into his hand. "What the hell is this?"

"Words on post-it notes?"

"Quit playing dumb with me, Sammy. I know what this is about. You're trying to play matchmaker with me and Cas, aren't you?" He didn't let his brother get a word in edgeways. "Sorry to disappoint, but it ain't working; I'm not gonna ask him."

Sam crossed his arms. "Why?"

"Why?"

"Yeah. You heard me. Why?"

"Because - He's - Y'know, he's -"

"What? Because he's a friend? I'm going with Charlie, and she's just a friend. We both know that."

"Yeah, but -"

"But, what? Can you actually think of a reason? Is it because he's a guy?" A smirk crossed his face. "Is it because you like him?"

"I don't -!"

"Dude, don't even try to deny it. We all know. We'd have to be idiots not to. And, to be honest, we're not bothered. Hell, the less detail I know about your love life, the better. Basically, the only thing standing in your way here is your masculinity issues - no change there, then." He clapped his silent, and slightly stunned, brother on the shoulder. "Go ask him. What's the worst that could happen, Deany?"

This nickname brought out expression on Dean's face again. "Never call me that again, Sammy."

"Sorry. I meant Jerk."

"Bitch."

* * *

Dean had to wait about half an hour before he stumbled upon Cas again. The angel had been coerced by Charlie into helping her hang more decorations in what she had started calling "the prom room". Already, everything was hidden under masses of streamers and lights, just like the rest of the bunker. The décor could actually put many high school proms to shame.

"Nice job." Dean nodded to the two decorators in turn.

"Hello, Dean." The angel appeared pleased to see him. "What can I do for you?"

"As a matter of fact, I was wondering if I could talk to you." He glanced at Charlie. "Y'know, alone?"

The redhead grinned triumphantly. "Oh, don't worry about me. I'll get out of your way." She clapped Cas on the shoulder as she went past, sidling out of the room and leaving the two men alone together.

"What do you wish to talk about?"

"So, um, I was thinking - This whole prom thing - Y'know, Sam and Charlie are technically going together, so - I was just wondering -"

"You were wondering if I would want to go with you," Cas finished for him. "I know."

"You don't have - Wait, what? How did you know?"

"Your notes led me to that conclusion." Cas reached into the pockets of his trenchcoat and brought out a large handful of pink post-it notes, smoothing out the creases with his fingers. The ones Dean hadn't ripped from his door when he'd found them. "Some of the words were missing, but I managed to work out the message behind them."

"Right." Dean shuffled awkwardly. "So - well, uh, what do you think?"

Cas pondered for less than a moment before he nodded. "Alright. I shall go with you."

"Really? - I mean, um, cool. Right. Yeah." Dean hid a wince. Damn, he was going to get Sam back for this. Or maybe buy him pie as a thank you. He wasn't entirely sure which yet.

* * *

"Isn't this great?" Charlie linked arms with Sam, gesturing to the other two men on the other side of the room. "They're finally, _finally_ , doing something."

The prom had been going on for the past two hours, and Dean had spent most of the time eating his way through the pie being provided and having sparse one sentence conversations with Cas, which wasn't sitting well with Charlie. She wasn't about to have her entire plan ruined by the two idiots now, especially after all her hard preparation, and so she'd switched the track from whatever upbeat rock song was playing to a soft piece of classical music, yelling "Slow dance!" as she did so, almost making Dean choke on his slice of pie (that seemed to be a recurring reaction every time Charlie mentioned something to do with this insane, makeshift prom). For the past three minutes, Dean and Cas had been awkwardly shuffling back and forth in time to Glenn Miller, talking quietly amongst themselves, whilst the younger Winchester and Charlie had watched on, in a mixture of impatience and anticipation.

"Are they ever going to give in?" Sam wondered aloud. Charlie was about to reply, when she held up a hand.

"Wait, wait, something's happening - what are they doing now?"

Cas had stopped following Dean's lead in their uncomfortable routine and placed his hands firmly on his shoulders. Whatever he was saying must have been fascinating, because Dean didn't seem to have any smart ass comments to interrupt with. In fact, if Sam was not mistaken, he had that same, slightly stunned expression on his face. It didn't last very long, however, as Dean seemed to come to his senses, grab Cas by the lapels of his trenchcoat and slam their lips together.

Charlie let out a muffled shriek at the sight, leaping up and down on one foot, breaking out into a round of applause, causing the kissing couple to break apart, suddenly remembering that they had an audience.

" _Finally_!" Sam was rolling his eyes up to the heavens, as if some great miracle had just occurred. "It took a reenactment of prom, but it finally happened! You guys finally admitted it!" He turned to Charlie, holding up a hand. "Hi-five, my fellow matchmaker." He continued to grin at his brother. "Told you we all knew it."

"Shut up, Sammy!" Dean yelled from the other side of the room, shaking his head.

His brother was _never_ going to let this one go.

* * *

 **Wow, this turned out to be two thousand words longer than I intended! But it was too much fun writing about Sam and Charlie's matchmaking schemes. I hope you enjoyed reading about them too. :)**


End file.
